


In the Attempt of Understanding

by figsforachilles



Category: Supernatural
Genre: Alternate Universe - High School, Artist Castiel (Supernatural), Friends to Lovers, Getting Together, M/M, Tutoring, Wrestler Dean Winchester
Language: English
Status: In-Progress
Published: 2021-02-04
Updated: 2021-02-06
Packaged: 2021-03-15 12:28:47
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,882
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29189322
Author URL: https://archiveofourown.org/users/figsforachilles/pseuds/figsforachilles
Summary: In his junior year of high school, Dean Winchester is failing algebra. He asks the quiet kid, Castiel, to tutor him. They get to know each other through their sessions, and feelings start to arise.
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 16





	1. Chapter 1

**Author's Note:**

> This is the first thing I'm publishing, so I hope you like it! I have the entire story planned out, and there is a lot more to come.

###  November 1995 

Dean was failing algebra. Bobby wasn’t the strictest father figure around, but there would be hell to pay if Dean dropped out of school after Bobby had given him a better shot at graduating. His options were limited. There was paying attention in class, but that was no good. Mr. Herskowitz smoked four packs a day. His classroom smelled like it and his voice spelled it out loud and clear, clearer than he had ever explained the quadratic formula. _I could ask Sam to show me_ , Dean thought. If he asked his younger brother, Dean would never hear the end of “How the hell do you not get the quadratic formula?”, so that was out of the question too.

Mr. Herskowitz squeezed through the rows of desks that were crammed into the room, handing back graded quizzes from last week to Dean’s classmates. Dean leaned back in his chair and groaned. It wouldn’t be good. Two desks ahead of him, then one, and then Mr. H put Dean’s quiz on his desk face down. That was never a good sign. Dean lifted up a corner of the paper. There was a bright red 64 staring at him, and Dean let go of the page, not bothering to turn it over completely. 

So much for Bobby giving him free reign of the Impala. He’d probably have to relinquish it until he could get his shit together. That had happened once before, soon after Bobby had rescued Sam and Dean from their father and taken them home with him to Sioux Falls. Dean had been pissed at himself for not being able to confront his father, for running away, even though Bobby had said it was the best thing for him and Sam.

The raspy voice of his teacher drew Dean out of his thoughts. “Mr. Novak, well done on the quiz last Friday,” Mr. Herskowtiz said to the boy sitting behind Dean. _Maybe he could help me_ , Dean thought to himself. _Would it be weird to ask him? I don’t even know his first name._ Dean turned to look at the boy. He raised his arm and yawned, twisting around in his seat to disguise the action as a stretch. The boy (Herskowitz had called him Novak) had his head down, focused on the back of his quiz. On the paper, his pencil moved and animals and figures took shape. It was like nothing Dean had seen before. 

“You make it seem so effortless,” Dean said. It had slipped out of his mouth. The boy looked up with his mouth open and eyes wide.

“Oh. Uh. Thanks,” he said. A smile flickered across his face and his eyes returned to the paper.

 _What was that?_ Dean was usually composed in social situations. Without even trying, the boy behind him had made Dean’s facade crumble. He balled up his miserable test and laid his head on his desk. Thoughts of fishing and the Impala floated through his mind, and he settled in for the rest of one very boring algebra class. 

The bell startled him awake when it rang out through the classroom. Dean shoved his papers from class into the front of his textbook. Denim brushed Dean’s side, and he looked to see who the culprit was. The boy who sat behind him was heading up to the front of the class. He was wearing the blue jeans that had brushed against Dean. He gripped his notebook to his chest tightly, like it was his heart and someone was trying to steal it. The small black book was full to bursting; the edges of the pages were wrinkled and colored. Dean furrowed his brows. Mr. Herskowitz’s eyes were glued to the boy, his lips pursed. _Glad I’m not the one having that talk,_ Dean thought. _I wonder what he did_.

  
  


Dean dropped his books onto the kitchen counter and headed for the fridge. He opened it, but didn’t get to see more than a glimpse of its contents before Bobby’s hand closed it. Dean sighed. _Here it comes_. He grabbed a glass of water so he would have something to distract himself from the talk he knew was coming. Dean leaned against the counter, and Bobby took a seat at the table.

“How was school?” Bobby asked. It wasn’t unusual for him to ask, but he had asked in his you’re-in-trouble-boy tone. Dean twisted his necklace between his index finger and his thumb. 

“Fine, I guess,” he said. The counter was cold against his back. “I didn’t do so hot on my math test.”

“Dean, I know school’s not easy for you. But you have options,” Bobby said.

“I guess. But why bother when I’ll just end up a hunter or dead in a ditch somewhere by 20?” Dean crossed his arms and brought one hand to his face, pulling it from his cheeks to his jaw to ground himself.

“You listen, boy. You don’t have to end up like that, like me and Ellen and Rufus. I don’t know what you want to do, but if you work for it you could do a hell of a lot more than end up dead in a ditch.” Bobby stood and made his way to the cabinet where they kept glasses. He poured himself a glass of water, but made no move to sit back down. 

“How am I supposed to be a normal person with a normal job when I know that I’m the only one who can protect everyone from what’s out there?” Dean said. His foot tapped on the floor. He wanted to get upstairs and put a record on. 

“Hey, what do you think I do on the weekends? You’re not the only one around here killing demons.” Bobby said. “Why don’t you look around for a tutor? You can worry about being a normal person later. Just get your grades up first.”

“Right,” Dean said and started towards the stairs.

“I wasn’t done, you idjit,” Bobby said. “Hand over the keys. I don’t want you heading out to the movies or a game every night until your grades are decent.”

Dean sighed. There was the kicker. He felt around in his pocket for the keys to the Impala and threw them to Bobby. He went up the stairs, raising his hand in a greeting to Sam as he passed his open door. Dean shut his door behind him, then went to put on a record. He had left his books downstairs, he realized. Well, they could wait until he went back down for dinner. _I guess I will have to ask that kid if he can help me_ , Dean thought, and the music played.

After dinner, Dean went to the bathroom to shave, even though he didn’t really need to. A plan was forming in his head for how he would ask that Novak kid to tutor him. He was good at talking to people, so surely he could ask a quiet kid to help him out with a couple math problems. 

“Hey, man, do you mind helping me with homework sometime? I know you’re pretty good at school since Mr. H doesn’t have a problem with making it known to the free world that you’re better than the rest of us,” Dean said while lathering up the shaving cream. He frowned at the mirror. “No, way too wordy.” 

Dean started dragging the razor down his face, pausing in between strokes to rinse it off. “So, do you actually like math, or are you just good at it? Hmm, that could work as a lead in,” he said. He took another few passes at his cheeks. “I personally hate it, but maybe you could help change that.” He raised an eyebrow at himself in the mirror. “Does that sound too much like flirting?” His reflection shrugged back at him. He rinsed his face off, and left the bathroom for his room. 

  
  


Aaron slapped Dean on the back as he walked past his desk.

“I’ll see you at wrestling,” he said, already halfway out the door. Dean nodded a goodbye to him. He began putting his papers into his textbook, slower than usual, careful. He was waiting for the class to be mostly empty before he asked the boy behind him for help. His classmates trickled out into the sea of students in the hallway, and soon there was only Dean and the boy behind him, who was still seated at his desk. His hand was moving quickly across his sketchbook. He hadn’t noticed the bell ring, he was too hung up in his drawing. Dean swung his leg so that he was sitting facing towards the boy, the back of his chair against his chest.

“I’m Dean,” he said. The boy’s eyes met Dean’s, but his head stayed tilted mostly down. It was like he was waiting for Dean to leave so he could get back to what he was doing. “What are you drawing?” Dean asked. He had meant to get straight to the point, but the way the boy’s hand clutched his pencil like his life depended on it intrigued him.

“My name is Castiel. And I’m working on a thumbnail for an art assignment,” the boy—Castiel—said. He put the pencil between the pages of the book and closed it. “What do you want?”

“Well, I’ve heard Mr. H saying how well you did on last week’s quiz or the homework or whatever. And I’m not too great at math,” Dean said. “Bobby, uh, my dad, took my car keys until I can get my grade up. So I was thinking maybe you could help me? All I see you do is draw, so I’m assuming you probably have some free time that you could spend teaching me.” Dean rubbed the back of his head sheepishly and looked down at the floor. Castiel’s fingers drummed on the cover of his sketchbook. 

“Yeah, okay,” Castiel said. There was a faint smile on his face. “But only if you’re not an asshole to me like some of your jock friends are.” 

Dean nodded, a smile on his face. “I can do that,” he said. “Thanks.”

“Tomorrow after school in the library?”

“Sounds good. See you then,” Dean said. He gathered his books in his arms and gave Castiel a curt nod, then joined the rest of the student body in the halls so he could begin the walk home.


	2. Chapter 2

Dean started gathering his books in his arms before the bell rang. Usually he hung back so he didn’t get caught in the throng of people rushing out to the great outdoors. But today he was getting tutored by Castiel. He wanted to avoid awkward small talk as much as possible, and he knew Castiel usually stayed for a few minutes after class to finish whatever he was working on. So he joined his classmates in pushing through the door into the hallway, and followed the flow of the foot traffic.

He stopped when someone tugged on the arm of his jacket. He turned, and there was Castiel, panting like he’d run to catch up to Dean. 

“You have been to the library before, right?” Castiel asked. He pushed his glasses up and readjusted the strap of his messenger bag. Dean felt blood rise to his cheeks.

“Of course I have. I was just getting a head start so we can get a good table,” Dean said. Castiel’s hand came to his mouth to stifle a small laugh. 

“Are you sure? Because you’re going the opposite direction of where it is.”

Dean’s mind raced, looking through the archives of his mind to see how he could get out of this as smoothly as possible. He didn’t want to look even dumber than he already did. Asking someone he barely knew to tutor him was bad enough, and now he had made it seem like his internal compass was broken. 

“Yeah, I just had to stop by my locker first to grab a pencil. I don’t do shit in class so I never have one on me,” Dean said. He fiddled with the amulet around his neck. 

“Dean, they have pencils in the library. Come on,” Castiel said, and started walking the other way. Dean kept close to him in the halls. He didn’t want someone else to squeeze between them and for him to get lost. In reality, he hadn’t been to the library before, at least not since his first day there when he’d been given a tour. At that point he hadn’t cared enough to pay attention to anything except where to eat and piss, and the location of a library that he had thought would never come into his sight again hadn’t exactly lodged itself in his long-term memory. 

Castiel wound through the halls, dodging people who were egotistic enough to stand in clusters in the middle of the hall and not move for students who needed to go to their next destination. Dean followed. He had to take longer strides than normal to keep up. Although he was a few inches taller than Castiel, the shy boy was confident in his path to the library and he walked fast. His heavy shoes made a nice noise against the school’s tile floor. Dean wondered if Castiel had practiced walking so fast in those shoes. He was sure that if he tried to speed through the school in shoes that looked like they weighed down Castiel’s entire body, he would’ve tripped in about five seconds.

Dean wouldn’t have known they had reached the library if he hadn’t just become intensely aware that he hadn’t put enough space between himself and Castiel to avoid a collision. Castiel had stopped without warning. Dean’s arms slammed into his stomach. His math book flew out of his arms and was sent upwards into his chin. Castiel’s sweater was pressed against Dean’s hands. It was incredibly soft. Dean stepped back. He kept his eyes away from Castiel’s face as he readjusted the things he was carrying. 

“Give me a warning next time you stop for no reason, would ya?” Dean said. 

“I thought you said you had been to the library before,” Cas said. The corners of his eyes crinkled when he smiled. Dean looked down at the floor and shook his head. “Well, first time for everything.” The door that looked like every other in the school. The only marker that it wasn’t a classroom was a small plaque above the door frame that was hard to read for how worn it was. It read “LIBRARY”. Cas pushed open the door, and led Dean into the library.

Inside, there were a few students at tables who were settling in to work. To the left of the door was a desk with school supplies on it—trays of lined and graph paper, a jar of pencils, and a sticky note dispenser were there, among other things.

“You can just use this stuff?” Dean asked. Castiel nodded.

“I have graph paper though, so just grab a pencil and a couple different colored highlighters and I’ll find us a table,” Castiel said. He slung his messenger bag off his shoulder and carried it, nearly dragging on the floor, to a table that was half-hidden behind a bookshelf. Dean took his time sharpening a pencil so that he wouldn’t have to get up too soon to sharpen it again. He picked a yellow and a green highlighter, then made his way over to the table that Castiel had laid out his homework onto.

The clock ticked on, and by the time their hour together had gone by Dean had erased so much of his paper that there were three holes in it.

“Did you learn anything, or is your skull too thick for polynomials to get in there?” Castiel asked. Dean rolled his eyes.

“Now I know that when you’re solving for shit you have to do the same thing on both sides,” he said. Castiel nodded. 

“What do you like? If you’re not studying, there must be something you do in your free time,” Castiel said. He flipped open his messenger bag, pulling the strap over his bag with one hand and putting a notebook into his bag with the other.

“I wrestle and I drive around listening to music,” Dean said. “Which is why I’m doing this in the first place, I need my Baby back.” He stuck in hand in the pocket of his leather jacket. It was muscle memory to grab his keys and then twirl them around his pointer finger. 

“What, you got banned from seeing your girlfriend until you can learn how the order of operations works?” Cas asked. 

“No, Baby’s my car. A ‘67 Chevy Impala. She’s beautiful,” Dean said. His eyes seemed brighter than before.

“I’m sure she is,” Castiel said.

Dean looked out the window. The school parking lot was mostly empty now. The cars of teachers who had stayed behind to grade were there, and athletes who hadn’t driven home yet because of practice. 

“Well, at least you have wrestling. That must take up some of your time,” Castiel said as he stood. Dean turned from the window and looked at his tutor. Though Castiel’s stature was small, in the low light of the library his presence seemed enormous. He was steady and quiet like a panther in the jungle who was watching its potential prey. Dean shivered. The window next to their table was open, and he went to close it.

“It’s not that often, just Monday and Wednesday. Sometimes we have matches on weekends. But yeah, it’s nice to feel powerful a couple times a week,” Dean said. “Thank you for helping me. I’m not sure I really get it yet, but it was easier with you there.” 

Cas smiled. “I’m glad I could help somewhat. We can keep working on it if you’d like, when you don’t have wrestling.”

“Sure,” Dean said. 

“My old man’s pretty strict on curfew, I have to be home for supper. But I’ll see you tomorrow, Dean.” With that, Castiel turned and started towards the library door. The librarian waved to him on the way out. Dean figured he must be on speaking terms with her. Castiel seemed like the type of person to have his nose stuck in a book all the time. Dean gathered his things, and returned to the winding halls of the school.

When Dean walked out the side door that put him on the street closest to home, Jo Harvelle’s truck was in the parking lot. Usually she would’ve been gone long ago, off to the movies with Charlie or Ash or both. Dean walked up to the truck’s passenger side door. Through the window, Jo was clutching the steering wheel with both hands. Her head rested on the wheel, her hair obscuring her face from Dean. He rapped on the truck’s red frame with his knuckles. She turned her head to see who was there. Her expression was tight with concern at the intrusion before softening before she registered that it was Dean. Her mouth melted into a smile.

The two had known each other since childhood. They had played with each other during the summers when John would ship Sam and Dean off to Bobby’s for a few weeks so he could go off doing God knows what. Jo had been there when Dean fell in a creek and scraped his knee so bad that he needed six stitches. Dean had been there when Jo realized she liked a girl not because she wanted pretty hair like hers but because she liked the girl attached to the hair. And after Bobby had rescued Sam and Dean, Jo had been there. 

Once he had joined wrestling, the other guys had constantly been asking about any girls he might like. Jo’s friends were always prancing around with a guy on their arm, running them around the school like they were in a dog show and their boyfriends were purebred prize winners. And so Dean and Jo had pretended, for a few weeks, to be enamored with each other like all the other horny teenagers at their school. It had satisfied the taunting laughs and whispers of the friends that had been forced upon the two of them by the societal hierarchy of school until the rumors started. That Dean had fucked a cheerleader behind the bleachers during phys ed, or that Jo had been flirting with a student teacher, twirling her hair and laughing at jokes. It was clear by then that their fake relationship was pointless. So they had staged a breakup in the cafeteria one day, and the rumors fell out of fashion. 

The locks on the truck’s doors went  _ clunk, clunk  _ as Jo unlocked them. Dean took the invitation and opened the passenger door. He used the running board as a step to help hoist himself up. Jo’s truck was too jacked up for Dean to step into it comfortably. He swung into the passenger seat and closed the door. Jo had gone back to looking at her steering wheel. She clutched it so tightly that her knuckles were white. 

“Hello, anybody in there?” Dean asked. Jo shook her head like a dog shaking its coat after getting a bath. It was what she did to clear her thoughts. She looked up at him.

“I don’t want to be at home right now,” she said. Dean slid his ring off his finger. He lifted Jo’s right hand off the steering wheel and put his ring in her palm. For years she had liked to play with it to calm herself down. “My mom thinks Ash likes me and she keeps telling me to go for it. It’s not like I can tell her I already have a girlfriend.”

“You and Ash hang out all the time anyway. Why does she care if you’re dating?” Dean asked.

“She just wants me to be happy. She means well, but God if she isn’t fucking annoying about it,” Jo said. 

“Screw her idea of happy. You and Charlie are happy. It must suck knowing she’s already gotten what she wants for you, just without knowing.”

Jo nodded. She sighed and gave Dean’s ring back to him.

“Thanks for checking in,” she said.

“Course,” Dean said. “Do you mind dropping me off?”

“No problem. By the way, how was your first session with artist boy?”

“It was fine. He asked about wrestling, I didn’t think he would be interested in it.”

“Did you learn anything?”

“He asked that too. Maybe you should be hanging out with him instead of me,” Dean said. “He can be as intense as you. I don’t think he meant to be, but when he stood up at the end…” Dean trailed off. He looked out the window as if he might catch a glimpse of the boy with black hair. Jo laughed almost under her breath.

“You seem like me when I first realized I was into Charlie,” Jo said.

“I do not,” Dean said. “I’m just tired. He’s weird.”

“Say what you like,” Jo said.

“Just start the truck,” Dean said, and Jo did.


End file.
